151710-38-2Relevant articles and documents
Hydrogen bonding in cyclic imides and amide carb-oxy-lic acid derivatives from the facile reaction of cis-cyclo-hexane-1,2-carb-oxy-lic anhydride with o- and p-anisidine and m- and p-amino-benzoic acids
Smith, Graham,Wermuth, Urs D.
, p. o327-o331 (2012/10/29)
The structures of the open-chain amide carb-oxy-lic acid rac-cis-2-[(2-meth-oxy-phen-yl)carbamo-yl]cyclo-hexane-1-carb-oxy-lic acid, C15H19NO4, (I), and the cyclic imides rac-cis-2-(4-meth-oxy-phen-yl)-3a,4,5,6,7,7a-hexa-hydro-isoindole-1,3-dione, C15H17NO3, (II), chiral cis-3-(1,3-dioxo-3a,4, 5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, C15H 15NO4, (III), and rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a- hexahydroisoindol-2-yl)benzoic acid monohydrate, C15H 15NO4·H2O, (IV), are reported. In the amide acid (I), the phenyl-carbamoyl group is essentially planar [maximum deviation from the least-squares plane = 0.060 (1) A for the amide O atom] and the mol-ecules form discrete centrosymmetric dimers through inter-molecular cyclic carbox-y-carboxy O - H...O hydrogen-bonding inter-actions [graph-set notation R 2 2(8)]. The cyclic imides (II)-(IV) are conformationally similar, with comparable benzene ring rotations about the imide N - Car bond [dihedral angles between the benzene and isoindole rings = 51.55 (7)° in (II), 59.22 (12)° in (III) and 51.99 (14)° in (IV)]. Unlike (II), in which only weak inter-molecular C - H...Oimide hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong inter-molecular carb-oxy-lic acid O - H...O hydrogen-bonding associations. With (III), these involve imide O-atom acceptors, giving one-dimensional zigzag chains [graph-set C(9)], while with the monohydrate (IV), the hydrogen bond involves the partially disordered water mol-ecule which also bridges mol-ecules through both imide and carboxy O-atom acceptors in a cyclic R 4 4(12) association, giving a two-dimensional sheet structure. The structures reported here expand the structural database for compounds of this series formed from the facile reaction of cis-cyclo-hexane-1,2-dicarb-oxy-lic anhydride with substituted anilines, in which there is a much larger incidence of cyclic imides compared to amide carb-oxy-lic acids.
Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams
Matsuki,Inoue,Ishida,Takeda,Nakagawa,Hino
, p. 9 - 18 (2007/10/02)
Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.
